613684-35-8Relevant academic research and scientific papers
Mamanuthaquinone: An antimicrobial and cytotoxic metabolite of Fasciospongia sp.
Christopher Swersey,Barrows, Louis R.,Ireland, Chris M.
, p. 6687 - 6690 (1991)
The isolation and structure elucidation of the novel sponge metabolite mamanuthaquinone 2 containing a rearranged drimane moiety linked to a benzoquinone are described. The absolute stereochemistry of 2 is determined via chemical modification, and its bio
Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis
Boufridi, Asmaa,Lachkar, David,Erpenbeck, Dirk,Beniddir, Mehdi A.,Evanno, Laurent,Petek, Sylvain,Debitus, Cécile,Poupon, Erwan
, p. 743 - 750 (2017)
Dactylospongia metachromia and Dactylospongia elegans collected from French Polynesia were studied with a particular focus on the variation of the diastereomeric ratio between ilimaquinone (4) and 5-epi-ilimaquinone (5). More than 100 samples, covering an area of 4100km2, were studied to try to clarify this intriguing issue. Nuclear magnetic resonance appeared as the non-destructive, straightforward technique of choice for a relative quantitative study. A random distribution, unique at that point in nature, is observed and leads to biosynthetic considerations. Biological evaluation of both compounds was also performed and showed moderate discrepancies in cytotoxicity and apoptosis induction.
A Ring-Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators
Evanno, Laurent,Lachkar, David,Lamali, Assia,Boufridi, Asmaa,Séon-Méniel, Blandine,Tintillier, Florent,Saulnier, Denis,Denis, Stéphanie,Genta-Jouve, Grégory,Jullian, Jean-Christophe,Leblanc, Karine,Beniddir, Mehdi A.,Petek, Sylvain,Debitus, Cécile,Poupon, Erwan
supporting information, p. 2486 - 2497 (2018/04/20)
We report herein a ring-distortion strategy applied to marine natural substances ilimaquinone and 5-epi-ilimaquinone. A chemically diverse library of molecules was synthesised that included rearrangements of the sesquiterpene moiety and original reorganisations of the quinone ring. Chemoinformatic analyses evaluated the rise of structural diversity and the exploration of chemical space. Some focussed biological activities of this library were also investigated; quorum sensing activity of Vibrio harveyi was envisaged and some of the new compounds were shown to be good quorum sensing inhibitor candidates, whereas others were activators. Toxicities were also evaluated and some products showed micromolar activities against human umbilical vein endothelium, human hepatocellular carcinoma and human lung carcinoma (A549) cells.
Determination of the absolute stereochemistry of cyclosmenospongine
Utkina, Natalia K.,Denisenko, Vladimir A.,Scholokova, Olga V.,Makarchenko, Aleksandra E.
, p. 1263 - 1265 (2007/10/03)
The absolute stereochemistry of the sponge metabolite cyclosmenospongine (1) was determined as 5R, 8S, 9R, 10S by chemical correlation. Substitution of the methoxyl group by an amino group in the cyclic product 3 of acid-catalyzed rearrangement of ilimaquinone (5) afforded cyclosmenospongine 1. Cyclosmenospongine was also obtained by acid-catalyzed cyclization of smenospongine (6).
